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Regioselective Direct C-H Arylations of Protected Uracils. Synthesis of 5- and 6-Aryluracil Bases
- 1.0361006 - ÚOCHB 2012 RIV US eng J - Journal Article
Čerňová, Miroslava - Čerňa, Igor - Pohl, Radek - Hocek, Michal
Regioselective Direct C-H Arylations of Protected Uracils. Synthesis of 5- and 6-Aryluracil Bases.
Journal of Organic Chemistry. Roč. 76, č. 13 (2011), s. 5309-5319. ISSN 0022-3263. E-ISSN 1520-6904
R&D Projects: GA MŠMT(CZ) LC06077
Institutional research plan: CEZ:AV0Z40550506
Keywords : pyrimidines * uracil * direct C-H arylations * palladium
Subject RIV: CC - Organic Chemistry
Impact factor: 4.450, year: 2011
A new regioselective synthesis of 5- and 6-aryluracil bases has been developed based on direct C-H arylations of diverse 1,3-protected uracils. Benzyl-protected uracils were selected as the most practical in terms of stability during the arylation and facile cleavage of the benzyl groups. Pd-catalyzed C-H arylations in absence of CuI gave preferentially 5-aryl-, whereas the reactions in presence of CuI gave 6-aryl-1,3-dibenzyluracils. Final deprotection either by transfer hydrogenolysis over Pd/C or by treatment with BBr3 gave the desired free arylated uracil bases in good yields.
Permanent Link: http://hdl.handle.net/11104/0198426
Number of the records: 1